CN107108497B - Compound for organic electric element, organic electric element using same, and electronic device using same - Google Patents

Compound for organic electric element, organic electric element using same, and electronic device using same Download PDF

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CN107108497B
CN107108497B CN201580055069.7A CN201580055069A CN107108497B CN 107108497 B CN107108497 B CN 107108497B CN 201580055069 A CN201580055069 A CN 201580055069A CN 107108497 B CN107108497 B CN 107108497B
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CN107108497A (en
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李范成
李善希
金大成
李允硕
李揆慜
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DukSan Neolux Co Ltd
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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    • Y02E10/549—Organic PV cells

Abstract

The present invention discloses a compound represented by chemical formula 1, an organic electric element including a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, and an electronic device using the organic electric element, wherein the organic layer includes the compound represented by chemical formula 1, so that the luminous efficiency and the lifetime of the element can be improved, and the driving voltage can be reduced.

Description

Compound for organic electric element, organic electric element using same, and electronic device using same
Technical Field
The present invention relates to a compound for an organic electric element, an organic electric element using the same, and an electronic device using the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic electric element utilizing an organic light emitting phenomenon generally has an anode, a cathode, and a structure including an organic layer therebetween. Here, the organic layer is generally formed as a multilayer structure composed of various different materials in order to improve efficiency and stability of the organic electric device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
In the organic electric element, materials used as the organic layer can be classified into a light emitting material and a charge transporting material according to functions, for example, a hole injecting material, a hole transporting material, an electron injecting material, and the like.
At present, the market of portable display screens has a tendency to increase their size to meet the demand of large-area display screens, and therefore, the power consumption of the portable display screens is higher than that of the conventional portable display screens. In this case, power consumption is a very important performance factor for portable display screens equipped with only a limited power supply source, a battery, and efficiency and lifetime issues must be addressed.
Efficiency, lifetime, driving voltage, and the like are related to each other, and when the efficiency is increased, the driving voltage is relatively decreased, and crystallization of an organic substance by Joule heating (Joule heating) occurring when driving is performed with the driving voltage being decreased is decreased, and finally, the lifetime tends to be improved. However, even if the organic layer is simply improved, the efficiency cannot be maximized. This is because both long life and high efficiency can be achieved only when the energy level and T1 value between the organic layers and the intrinsic properties (mobility, surface properties, etc.) of the substance are optimally combined.
In recent general organic electroluminescent elements, it is preferable to provide an emission assisting layer between the hole transporting layer and the light emitting layer in order to solve the problem of light emission in the hole transporting layer, and it is necessary to develop different emission assisting layers for the respective light emitting layers (R, G, B).
Generally, electrons (electrons) are transferred from the electron transport layer to the light emitting layer, holes (holes) are transferred from the hole transport layer to the light emitting layer, and excitons (exitons) are generated by recombination (recombination).
However, the substance used for the hole transport layer should have a low Highest Occupied Molecular Orbital (HOMO) value and thus mostly have a low T1 value, whereby excitons (exitons) generated in the light emitting layer are transferred to the hole transport layer, eventually causing charge imbalance (charge imbalance) in the light emitting layer to emit light in the hole transport layer or at the interface of the hole transport layer, so that the phenomena of reduced color purity, reduced efficiency, and shortened lifetime are exhibited.
In addition, when a substance having a high hole mobility (hole mobility) is used in order to realize a low driving voltage, the efficiency tends to decrease due to the substance. This is because, in a general organic electroluminescent element, hole mobility (hole mobility) is faster than electron mobility (electron mobility), resulting in internal charge imbalance (charge imbalance) of a light emitting layer, which results in a decrease in efficiency and lifetime.
Therefore, the light-emission auxiliary layer should have a hole mobility (in the range of blue element driving voltage of all devices) and a high T at an appropriate driving voltage capable of solving the above-mentioned problems of the hole transport layer and the like1(electron block) value, wide band gap (wide band gap). However, this cannot be simply constituted by the structural characteristics of the core of the substance of the light-emitting auxiliary layer, and is possible when the core of the substance and the characteristics of the Sub (Sub) -light-emitting layer are combined. Therefore, in order to improve the efficiency and life of organic electric elements, it is highly desirable to have a high T1And a wide band gap.
That is, in order to fully utilize the excellent characteristics of the organic electric element, materials constituting the organic layer in the element, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, a light emitting auxiliary layer material, etc., have been supported by stable and efficient materials, but development of an effective organic layer material for a stable and efficient organic electric element has not been fully developed so far. Therefore, there is a continuing need to develop new materials, and in particular, there is an urgent need to develop materials for luminescence auxiliary layers.
Disclosure of Invention
The invention aims to provide a compound capable of reducing driving voltage and improving luminous efficiency, color purity and service life, an organic electric element using the compound and an electronic device thereof.
In one embodiment, the present invention provides a compound represented by the following chemical formula 1:
chemical formula 1:
Figure BDA0001266354490000031
in another embodiment, the present invention provides an organic electric element using the compound represented by the above chemical formula and an electronic device thereof.
By using the compound of the embodiment of the invention, the driving voltage of the element can be reduced, and the luminous efficiency, the color purity and the service life of the element can be greatly improved.
Drawings
Fig. 1 is an illustrative view of an organic electroluminescent element according to the present invention.
Description of reference numerals
100: the organic electric element 110: substrate
120: first electrode 130: hole injection layer
140: hole transport layer 141: buffer layer
150: light-emitting layer 151: luminescence auxiliary layer
160: electron transport layer 170: electron injection layer
180: second electrode
Detailed Description
Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.
In the process of attaching reference numerals to the components in each drawing, it is to be noted that the same components are given the same reference numerals as much as possible even when they are shown in different drawings. In describing the present invention, a detailed description will be omitted in a case where it is determined that a detailed description of a related well-known structure or function would obscure the gist of the present invention.
In describing the components of the present invention, terms such as first, second, A, B, (a), (b), and the like may be used. Such terms are merely used to distinguish one structural element from another structural element, and the nature, order, sequence, or the like of the related structural elements are not limited by such terms. In the case where one component is "connected", "coupled" or "coupled" to another component, the component may be directly connected or coupled to the other component, but it is also understood that other components may be "connected", "coupled" or "coupled" between the components.
When a component such as a layer, a film, a region, or a plate is located "on" or "on" another component, this is understood to mean that the component is located "directly above" the other component, and that the component may also be located in the middle of the other component. Conversely, when a structural element is located "directly above" another part, it is to be understood that there is no other part in the middle.
Unless otherwise indicated, the following terms used in the present specification and the appended claims have the following meanings.
The term "halo" or "halogen" used in the present specification is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise specified.
The term "alkane" or "alkyl" as used in the present invention, is a single bond having a carbon number of 1 to 60, and means a radical containing a saturated aliphatic functionality of a straight-chain alkyl group, a molecular chain alkyl group, a cycloalkyl (alicyclic), a cycloalkyl substituted by an alkane, an alkyl substituted by a cycloalkyl.
The term "haloalkyl" or "haloalkyl" as used herein, unless otherwise specified, denotes an alkyl group substituted with a halogen.
The term "alkenyl" or "alkynyl" used in the present invention has a double bond or a triple bond having a carbon number of 2 to 60, respectively, and includes a straight chain type or a side chain type chain group, unless otherwise specified, but is not limited thereto.
The term "cycloalkyl" used in the present invention means, unless otherwise specified, an alkane forming a ring having a carbon number of 3 to 60, but is not limited thereto.
The term "alkoxy", "alkoxy" or "alkoxy" used in the present invention means an alkyl group to which an oxygen radical is attached, and has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.
The term "aryloxy" or "aryloxy" as used in the present invention means an aryl group to which an oxygen radical is attached, and has a carbon number of 6 to 60 as long as there is no other description, but is not limited thereto.
Unless otherwise stated, the term "fluorenyl" or "fluorenylvinyl" as used in the present invention means a 1-or 2-valent functional group in which both R, R ' and R "are hydrogen in the following structures, respectively, and" substituted fluorenyl "or" substituted fluorenylvinyl "means that at least one of the substituents R, R ', R" is a substituent other than hydrogen, and includes the case where R and R ' combine to form a spiro compound together with the carbon to which they are bound.
Figure BDA0001266354490000051
The terms "aryl" and "arylene" used in the present invention have a carbon number of 6 to 60, respectively, unless otherwise specified, but are not limited thereto. In the present invention, the aryl group or arylene group includes monocyclic type, ring aggregate, fused polycyclic and spiro compounds, and the like.
The term "heterocyclic group" used in the present invention includes not only aromatic rings such as "heteroaryl" or "heteroarylene", but also non-aromatic rings, and unless otherwise specified, means rings of 2 to 60 carbon atoms each including one or more heteroatoms, but the present invention is not limited thereto. The term "heteroatom" used in the present specification means N, O, S, P or Si unless otherwise specified, and the heterocyclic group means a monocyclic type, a ring aggregate, a fused polycyclic and spiro compound containing a heteroatom, and the like.
Also, "heterocyclic group" may include SO-containing carbon atoms in addition to the carbon atoms forming the ring2Of (2) a ring of (a). For example, "heterocyclyl" includes the following compounds.
Figure BDA0001266354490000052
In the present specification, a functional group having a valence of 1 or 2 is named as a functional group name, or a parent compound is named by labeling a valence number. For example, "2-valent benzothiophene" means a 2-valent functional group of benzothiophene as a parent compound, and similarly, "2-valent dibenzothiophene" means a 2-valent functional group of dibenzothiophene as a parent compound, "2-valent furan" means a 2-valent functional group of furan as a parent compound, "2-valent dibenzofuran" means a 2-valent functional group of dibenzofuran as a parent compound, and "2-valent pyrimidine" means a 2-valent functional group of pyrimidine as a parent compound. Similarly, a 3-valent functional group can also be represented by showing a 3-valent state before the parent compound, for example, "3-valent aryl" represents a 3-valent functional group that is an aromatic aryl group, and "3-valent fluorene" represents a 3-valent functional group of fluorene.
The term "ring" as used in the present invention includes single-and multi-chain and heterocyclic rings, which contain not only hydrocarbon rings but also at least one heteroatom, and also aromatic and non-aromatic rings.
The term "multi-chain" as used in the present invention includes ring aggregates (rings) such as biphenyls and terphenyls, fused polycyclic and spiro compounds, including not only aromatic but also nonaromatic, and hydrocarbon rings including heterocyclic rings containing at least one heteroatom.
The term "ring aggregates" as used in the present invention means that two or more rings (monocyclic or fused rings) are bound to each other by a single bond or a double bond, and the number of direct links between such rings is one less than the total number of rings contained in such a compound. The ring aggregates may be directly connected to each other by single or double bonds from the same or different rings.
The term "fused polycyclic group" as used in the present invention means a fused ring form shared by at least two atoms, and includes a fused ring form of two or more hydrocarbons and a fused ring form of at least one heterocyclic group containing at least one hetero atom. Such fused polycyclic rings may be aromatic rings, heteroaromatic rings, aliphatic rings, or a combination of these rings.
The term "spiro compound" used in the present invention means "spiro union (spiro union)", and spiro union means that only one atom is shared by two rings, thereby achieving linkage. In this case, the atoms shared between the two rings are referred to as "spiro atoms", and depending on the spiro atoms included in one compound, these are referred to as "monoazo-", "diazo-", and "trispiro-" compounds, respectively.
In the case where the prefix is named consecutively, it means that the substituents are listed in the order of description first. For example, in the case of aralkyloxy, alkoxy substituted by aryl, in the case of alkoxycarbonyl, carbonyl substituted by alkoxy, and in the case of arylalkenyl, alkenyl substituted by arylcarbonyl, which is carbonyl substituted by aryl, are meant.
Also, unless otherwise specified, in the term "substituted or unsubstituted" used in the present invention, "substituted" means selected from the group consisting of deuterium, halogen, amino group, nitrile group, nitro group, and C1-C20Alkyl of (C)1-C20Alkoxy group of (C)1-C20Alkyl amine of (C)1-C20Alkyl thiophene of (2), C6-C20Arylthiophene of (2), C2-C20Alkenyl of, C2-C20Alkynyl of (A), C3-C20Cycloalkyl of, C6-C20Aryl, fluorenyl, by heavy hydrogenSubstituted C6-C20Aryl of (C)8-C20And C comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P2-C20Is substituted with at least one substituent of the group consisting of heterocyclic groups of (a) but is not limited to these substituents.
The chemical formula used in the present specification can be applied similarly to the definition of the substituent defined by the index of the following chemical formula unless otherwise specified.
Figure BDA0001266354490000061
Wherein, in the case where a is an integer of 0, the substituent R1Absent, one substituent R in the case where a is an integer of 11Combined with one of the carbons for forming the benzene ring, in the case where a is an integer of 2 or 3, in such a manner that R is present1Which may be the same or different, in the case where a is an integer of 4 to 6, are bonded to the carbon of the benzene ring in a similar manner, on the other hand, the representation of hydrogen bonded to the carbon for forming the benzene ring is omitted.
Figure BDA0001266354490000071
Fig. 1 is an exemplary view of an organic electric element according to an embodiment of the present invention.
Referring to fig. 1, an organic electric element 100 according to an embodiment of the present invention includes: the first electrode 120 is formed on the substrate 110; a second electrode 180; and an organic layer containing the compound of the present invention between the first electrode 120 and the second electrode 180. At this time, the first electrode 120 may be an Anode, the second electrode 180 may be a Cathode, and in the case of an inverted type, the first electrode may be a Cathode and the second electrode may be an Anode.
The organic layer may include a hole injection layer 130, a hole transport layer 140, an emission layer 150, an electron transport layer 160, and an electron injection layer 170 in this order on the first electrode 120. At this time, at least one of these layers may not be formed, and may include a hole blocking layer, an electron blocking layer, the light emission assisting layer 151, the buffer layer 141, and the like, or the electron transport layer 160 and the like may perform the function of the hole blocking layer.
In addition, although not shown, the organic electric element according to an embodiment of the present invention may further include a protective layer or a light efficiency improving layer (Capping layer) formed on a surface opposite to the organic layer, among at least one surface of the first electrode and the second electrode.
The compound of an embodiment of the present invention suitable for the above organic layer may be used as a material of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, the host (host) or dopant (dopant) of the light emitting layer 150, or the light efficiency improving layer. For example, the compound of the present invention can be used as the light-emitting layer 150, the hole transport layer 140, and/or the light-emission auxiliary layer 151.
On the other hand, even if the same core is used, the band gap (band gap), the electrical characteristics, the interface characteristics, and the like are different depending on which substituent is bonded to which position, and therefore, it is necessary to study the selection of the core and the combination of the Sub (Sub) -substituent to which the core is bonded, and in particular, when the energy level and the T1 value between the organic layers, the intrinsic characteristics of the substance (mobility, interface characteristics, and the like), and the like constitute an optimum combination, both long life and high efficiency can be achieved.
As described above, in recent years, in order to solve the problem of light emission in the hole transport layer of the organic electroluminescent element, it is preferable to form a light emission auxiliary layer between the hole transport layer and the light emitting layer, and it is necessary to develop different light emission auxiliary layers for the respective light emitting layers (R, G, B). On the other hand, in the case of the light-emitting auxiliary layer, since it is necessary to analyze the mutual relationship between the hole transport layer and the light-emitting layer (host), even if the same core is used, if the organic layers used are different, it is difficult to draw the characteristics thereof.
Accordingly, in the present invention, the hole transport layer and/or the light emission auxiliary layer are formed by using the compound represented by chemical formula 1 such that each organic layer is formedEnergy level between layers, T1The value and the intrinsic properties (mobility, interface properties, etc.) of the substance are optimized, so that the lifetime and efficiency of the organic electric element can be improved.
The organic electroluminescent device according to an embodiment of the present invention can be manufactured by using various evaporation methods (deposition). The anode 120 may be formed by depositing metal, a metal oxide having conductivity, or an alloy thereof on a substrate, and an organic layer including the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, the electron transport layer 160, and the electron injection layer 170 is formed thereon, and then a substance capable of functioning as the cathode 180 is deposited thereon. Also, a light emission auxiliary layer 151 may be additionally formed between the hole transport layer 140 and the light emitting layer 150.
The organic layer is formed using a plurality of polymer materials, and a smaller number of layers are formed by a solution process (solvent process) other than the vapor deposition method, for example, a spin coating process, a nozzle printing process, an ink jet printing process, a slit coating process, a dip coating process, a roll-to-roll process, a doctor blade process, a screen printing process, a thermal transfer method, or the like. Since the organic layer of the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.
The organic electric element according to an embodiment of the present invention may be classified into a front emission type, a rear emission type, or a double-sided emission type according to the material used.
White Organic Light Emitting Devices (WOLEDs) have advantages of easy realization of high resolution and excellent process characteristics, and can be manufactured using conventional color filter technology of Liquid Crystal Displays (LCDs). Various structures of white organic light emitting elements mainly used for backlight devices are being proposed and patented. Typically, the present invention is applicable to such a white organic electroluminescent device, for example, a side-by-side (r) (red), g (green), and B (blue) light emitting parts arranged in parallel with each other in a planar manner, a lamination (stacking) system in which R, G, B light emitting layers are laminated one on top of the other, a Color Conversion Material (CCM) system in which blue (B) organic light emitting layers are used for electroluminescence and photoluminescence (phosphor) using inorganic phosphors are used for light emission therefrom, and the like.
The organic electric element according to an embodiment of the present invention may be one of an organic electroluminescence element, an organic solar cell, an organic photoreceptor, an organic transistor, and an element for monochromatic or white illumination.
Another embodiment of the present invention may include an electronic device, comprising: a display device including the organic electric element of the present invention; and a control section for controlling the display device. In this case, the electronic device may be a current or future wireless communication terminal, and may include all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigator, a game machine, various TVs, various computers, and the like.
Hereinafter, a compound according to an embodiment of the present invention will be described.
The compound of one embodiment of the present invention is represented by the following chemical formula 1.
< chemical formula 1>
Figure BDA0001266354490000091
In the above chemical formula, each symbol can be defined as follows.
In the above chemical formula 1, A and B are independently selected from the group consisting of the following chemical formula 1-1, chemical formula 1-2 and chemical formula 1-3, except for the case where A and B are preferably both chemical formulas 1-3. And preferably Ar is Ar in the case where A is the above chemical formula 1-11To Ar3Is phenyl and L1The case of m-phenylene (meta-phenylene) may be excluded.
Figure BDA0001266354490000092
In the above chemical formula 1, the formulaIn chemical formula 1-1 and chemical formula 1-2, Ar1To Ar4Independently of one another, from the group: c6-C60Aryl group, fluorenyl group, C containing at least one hetero atom selected from the group consisting of O, N, S, Si and P2-C60Heterocyclic group of (A), C3-C60And C is an aliphatic ring6-C60Condensed ring group of aromatic ring of-L' -N (R)a)(Rb) And combinations of these, in which case Ar2And Ar3Nitrogen (N) capable of binding and forming a ring together therewith.
Preferably, Ar1To Ar4Independently of each other may be C6-C25Aryl, fluorenyl or C3-C16And the like, and preferably may be C6、C10、C12、C14Aryl of (C)5、C12The heterocyclic group of (b) may be specifically a naphthyl group, a biphenyl group, a phenanthryl group, a methyl group, or a fluorenyl group substituted or unsubstituted with a phenyl group, a spirobifluorenyl group, a pyridyl group, a dibenzothienyl group or the like.
Preferably, Ar is1To Ar4Independently of one another, can be substituted by one or more substituents selected from the group consisting of: heavy hydrogen, halogen, silyl, siloxane, boron, germanium, cyano, nitro, C1-C20Alkylthio of, C1-C20Alkoxy group of (C)1-C20Alkyl of (C)2-C20Alkenyl of, C2-C20Alkynyl of (A), C6-C20Aryl of (2), C substituted by deuterium6-C20Aryl group, fluorenyl group, C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P2-C20Heterocyclic group of (A), C3-C20Cycloalkyl of, C7-C20Arylalkyl of, and C8-C20An aralkenyl group of (a).
In the above chemical formulas 1-1,1-2 and 1-3, L1To L3Can be selected, independently of one another, from the following groups: single bond, C6-C60Arylene group, fluorenylene group, C3-C60And C is an aliphatic ring6-C60A condensed ring group of the aromatic ring of (1), C containing at least one hetero atom of O, N, S, Si and P2-C60And heteroaryl groups consisting of these.
Preferably, L is as defined above1To L3Can be independently composed of single bond and C6-C18Arylene, fluorenylene or C3-C12And the like, and preferably may be C6Arylene group of (a), C5,C12The heterocyclic group of (b) may specifically be a fluorenylvinyl group, spirobifluorenyl group, pyridinylene group, dibenzothienyl group, or a combination of these, which may be substituted or unsubstituted with a single bond, phenylene, methyl or phenyl, or the like.
Preferably, L is as defined above1To L3Independently of one another, can be substituted by one or more substituents selected from the group consisting of: heavy hydrogen, halogen, silyl, siloxane, boron, germanium, cyano, nitro, C1-C20Alkylthio of, C1-C20Alkoxy group of (C)1-C20Alkyl of (C)2-C20Alkenyl of, C2-C20Alkynyl of (A), C6-C20Aryl of (2), C substituted by deuterium6-C20Aryl group, fluorenyl group, C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P2-C20Heterocyclic group of (A), C3-C20Cycloalkyl of, C7-C20Arylalkyl of, and C8-C20An aralkenyl group of (a).
In the above chemical formulas 1-1,1-2 and 1-3, L1To L3Can be selected, independently of one another, from the following groups: single bond, C6-C60Arylene group, fluorenylene group, C3-C60And C is an aliphatic ring6-C60A condensed ring group of the aromatic ring of (1), C containing at least one hetero atom of O, N, S, Si and P2-C60And heteroaryl groups consisting of these.
In the aboveIn the chemical formulae 1,1-1,1-2 and 1-3, R1To R16Can be selected, independently of one another, from the following groups: hydrogen, deuterium, halogen, C6-C60Aryl group, fluorenyl group, C containing at least one hetero atom selected from the group consisting of O, N, S, Si and P2-C60Heterocyclic group of (A), C3-C60And C is an aliphatic ring6-C60Condensed ring group of aromatic ring of (2), C1-C50Alkyl of (C)2-C20Alkenyl of, C2-C20Alkynyl of (A), C1-C30Alkoxy and C6-C30Aryloxy group of, -L' -N (R)a)(Rb) And a group consisting of these. In this case, R1To R16At least one ring can be formed by bonding adjacent groups to each other together with the benzene ring bonded thereto.
Preferably, R1To R16At least one ring can be formed by bonding adjacent groups to each other together with the benzene ring bonded thereto. For example, R1And R2、R2And R3、R3And R4、R5And R6、R6And R7、R7And R8、R9And R10、R10And R11、R11And R12、R13And R14、R14And R15And/or R15And R16Are bonded to each other so as to form at least one ring together with the benzene ring bonded thereto. That is, at least one pair of adjacent groups are bonded to each other to form a ring. For example, R1And R2Can be bonded to each other to form a ring such as naphthalene together with the benzene ring bonded thereto, R3To R16The same ring can be formed.
Preferably, R does not form a ring1To R16Independently of one another, may be hydrogen or C6-C18And the like, and preferably may be C6The aryl group of (2) may specifically be hydrogen or phenyl, etc.
Preferably, R is as defined above1To R16Independently of one another, can be substituted by one or more substituents selected from the group consisting of: heavy hydrogen, halogen, silyl, siloxane, boron, germanium, cyano, nitro, C1-C20Alkylthio of, C1-C20Alkoxy group of (C)1-C20Alkyl of (C)2-C20Alkenyl of, C2-C20Alkynyl of (A), C6-C20Aryl of (2), C substituted by deuterium6-C20Aryl group, fluorenyl group, C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P2-C20Heterocyclic group of (A), C3-C20Cycloalkyl of, C7-C20Arylalkyl of, and C8-C20An aralkenyl group of (a).
Preferably, L is as defined above1To L3Independently of one another, can be substituted by one or more substituents selected from the group consisting of: heavy hydrogen, halogen, silyl, siloxane, boron, germanium, cyano, nitro, C1-C20Alkylthio of, C1-C20Alkoxy group of (C)1-C20Alkyl of (C)2-C20Alkenyl of, C2-C20Alkynyl of (A), C6-C20Aryl of (2), C substituted by deuterium6-C20Aryl group, fluorenyl group, C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P2-C20Heterocyclic group of (A), C3-C20Cycloalkyl of, C7-C20Arylalkyl of, and C8-C20An aralkenyl group of (a).
The above L' is selected from the group consisting of: single bond, C6-C60Arylene group, fluorenylene group, C3-C60And C is an aliphatic ring6-C60And C containing at least one hetero atom selected from the group consisting of O, N, S, Si and P2-C60R is as defined aboveaAnd RbIndependently of one another, from the group: c6-C60Aryl, fluorenyl, C3-C60And C is an aliphatic ring6-C60And C containing at least one hetero atom selected from the group consisting of O, N, S, Si and P2-C60The heteroaryl group of (a).
Specifically, the following chemical formulas 2 to 9 show the case where chemical formulas 1-1,1-2 and 1-3 are independently bonded to A and B of the above chemical formula 1.
Figure BDA0001266354490000111
Figure BDA0001266354490000121
In the above chemical formulas 2 to 9, Ar1To Ar4,L1To L3And R1To R16May be the same as defined in the above chemical formula 1,1-1,1-2, 1-3.
Specifically, the above chemical formula 1 may be one of the following compounds.
Figure BDA0001266354490000131
Figure BDA0001266354490000141
Figure BDA0001266354490000151
Figure BDA0001266354490000161
Figure BDA0001266354490000171
Figure BDA0001266354490000181
Figure BDA0001266354490000191
As still another embodiment, the present invention provides a compound for an organic electric element represented by the above chemical formula 1.
In another embodiment, the present invention provides an organic electric element containing the compound represented by the above chemical formula 1.
At this time, the organic electric element may include a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, the organic layer may include the compound represented by chemical formula 1, and the compound represented by chemical formula 1 may be included in at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, or a light emitting layer of the organic layer. That is, the compound represented by the above chemical formula 1 may be used as a material of a hole injection layer, a hole transport layer, a light emission auxiliary layer, or a light emitting layer. Preferably, the compound represented by chemical formula 1 may be used as the material of the above-described luminescence auxiliary layer.
Preferably, an organic electric element including the compound represented by the above chemical formula 2 to chemical formula 9 in an organic layer is provided.
Preferably, an organic electric element comprising one of the above-described compounds 1-1 to 1-28, 2-1 to 2-28, 3-1 to 3-28, 4-1 to 4-16, 5-1 to 5-16, 6-1 to 6-12, 7-1 to 7-8, and 8-1 to 8-8 in an organic layer is provided.
Preferably, the organic layer may include 1 single or 2 or more compounds represented by the above chemical formula 1. For example, the light-emission auxiliary layer in the organic layer may be formed of the compound 1-1 alone, or may be formed of a mixture of the compound 1-1 and the compound 1-2.
On the other hand, the organic layer can be formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slit coating process, a dip coating process, or a roll-to-roll process.
In another embodiment of the present invention, the organic electric element further includes a light efficiency improving layer formed on at least one of a side of the first electrode opposite to the organic layer or a side of the second electrode opposite to the organic layer. Preferably, the light efficiency improving layer may include a compound represented by chemical formula 1.
In yet another embodiment of the present invention, the present invention provides an electronic device, including: a display device having an organic electric element including the organic layer; and a control section for driving the display device. In this case, the organic electric element of the present invention may be at least one of an organic electroluminescent element, an organic solar cell, an organic photoreceptor, an organic transistor, and an element for monochromatic or white illumination.
The following examples are given to specifically describe examples of synthesis of the compound represented by chemical formula 1 and examples of production of an organic electric device according to the present invention, but the present invention is not limited to the following examples.
Synthesis example
As an example, the compound (Product) represented by chemical formula 1 according to the present invention is prepared by reacting Sub1 with Sub 2 as in chemical formula 1 below, but is not limited thereto.
< reaction formula 1>
Figure BDA0001266354490000211
< reaction formula 2>
Figure BDA0001266354490000212
Example of Synthesis of sub1
The Sub1 of the above reaction formula 1 can be synthesized by the reaction pathway of the following reaction formula 2, but is not limited thereto.
< reaction formula 2>
Figure BDA0001266354490000213
Synthesis example of Sub1-2
1) Synthesis of Sub1-2(1) (A of chemical formula 1 is chemical formula 1-1, L)1Is a single bond)
Figure BDA0001266354490000214
Adding Sub 1-1(6.3g, 20mmol), Sub 1-1-1(3.4g, 20mmol), Pd2(dba)3(0.5g、0.6mmol)、P(t-Bu)3(0.2g, 2mmol), t-BuONa (5.8g, 60mmol), and toluene (300mL), followed by reaction at a temperature of 100 ℃. When the reaction is complete, CH is used2Cl2Extracting with water, and then, extracting with MgSO4The organic layer was dried and concentrated, and the resultant organic material was subjected to silicagel column and recrystallization to obtain the product Sub1-2(1) (yield: 76%) 6.1 g.
2) Synthesis of Sub1-2(2) (A of the formula 1 is a formula 1-1, L)1In the case of not a single bond)
Figure BDA0001266354490000221
Sub 1-1(5.0g, 16mmol), Sub 1-1-2(6.7g, 18mmol), Pd (PPh)3)4(0.06g、0.05mmol)、K2CO3(6.6g, 48mmol) was dissolved in anhydrous THF and a small amount of water, and the reaction was allowed to form a loop for 24 hours. When the reaction is completed, the temperature of the reaction product is lowered to normal temperature, and CH is used2Cl2Extraction was performed and washed with water. Using anhydrous MgSO4After a small amount of water was removed and the filtrate was filtered under reduced pressure, the product produced by concentrating the organic solvent was separated by column chromatography to obtain 5.6g of the desired product Sub1-2(2) (yield: 7)4)。
3) Synthesis of Sub1-2(3) (in the case where A of chemical formula 1 is chemical formula 1-2)
Figure BDA0001266354490000222
Mixing Sub 1-1(5.0g, 16mmol), Sub 1-1-3(8.0, 18mmol), Pd (PPh)3)4(0.06g、0.05mmol)、K2CO3(6.6g, 48mmol) was dissolved in anhydrous THF and a small amount of water, and the above-mentioned synthesis method of Sub1-2(2) was used to obtain 6.3g (yield: 71%) of the product Sub1-2 (3).
4) Synthesis of Sub1-2(4) (A of chemical formula 1 is chemical formula 1-3, L)3Is a single bond)
Figure BDA0001266354490000231
Adding Sub 1-1(6.3g, 20mmol), Sub 1-1-4(3.3g, 20mmol), Pd2(dba)3(0.5g、0.6mmol)、P(t-Bu)3(0.2g, 2mmol), t-BuONa (5.8g, 60mmol) and toluene (300mL) were synthesized by the above-mentioned Sub1-2(1) synthesis method to obtain the product Sub1-2(4) 6.0g (yield: 75%).
5) Synthesis of Sub1-2 (5) (A of chemical formula 1 is chemical formula 1-3, L)3In the case of not a single bond)
Figure BDA0001266354490000232
Mixing Sub 1-1(5.0g, 16mmol), Sub 1-1-5(6.6g, 18mmol), Pd (PPh)3)4(0.06g、0.05mmol)、K2CO3(6.6g, 48mmol) was dissolved in anhydrous THF and a small amount of water, and the above-mentioned synthesis method of Sub1-2(2) was used to obtain 5.5g (yield: 72%) of the product Sub1-2 (5).
Synthesis example of Sub1-3
When B of chemical formula 1 is chemical formula 1-1, the Sub1-3 can be synthesized by the synthesis methods of the above-mentioned Sub1-2(1) and Sub1-2(2), when B of chemical formula 1 is chemical formula 1-2, the above-mentioned Sub1-2(3), and when B of chemical formula 1 is chemical formula 1-3, the above-mentioned Sub1-2(4) and Sub1-2 (5).
The following examples of Sub1-3 are not intended to limit the present invention, and the FD-MS values are shown in table 1 below.
Figure BDA0001266354490000241
Figure BDA0001266354490000251
[ TABLE 1]
Compound (I) FD-MS Compound (I) FD-MS
Sub 1-3(1) m/z＝490.10(C30H23BrN2＝491.42) Sub 1-3(2) m/z＝642.17(C42H31BrN2＝643.61)
Sub 1-3(3) m/z＝492.09(C28H21BrN4＝493.40) Sub 1-3(4) m/z＝566.14(C36H27BrN2＝567.52)
Sub 1-3(5) m/z＝642.17(C42H31BrN2＝643.61) Sub 1-3(6) m/z＝742.20(C50H35BrN2＝743.73)
Sub 1-3(7) m/z＝742.20(C50H35BrN2＝743.73) Sub 1-3(8) m/z＝946.29(C66H47BrN2＝948.00)
Sub 1-3(9) m/z＝564.12(C36H25BrN2＝565.50) Sub 1-3(10) m/z＝640.15(C42H29BrN2＝641.60)
Sub 1-3(11) m/z＝565.12(C35H24BrN3＝566.49) Sub 1-3(12) m/z＝670.11(C42H27BrN2S＝671.65)
Sub 1-3(13) m/z＝640.15(C42H29BrN2＝641.60) Sub 1-3(14) m/z＝740.18(C59H33BrN2＝741.71)
Sub 1-3(15) m/z＝740.18(C50H33BrN2＝741.71) Sub 1-3(16) m/z＝944.28(C66H45BrN2＝945.98)
Sub 1-3(17) m/z＝538.10(C34H23BrN2＝539.46) Sub 1-3(18) m/z＝640.15(C42H29BrN2＝641.60)
Sub 1-3(19) m/z＝489.08(C29H20BrN3＝490.39) Sub 1-3(20) m/z＝564.12(C36H25BrN2＝565.50)
Sub 1-3(21) m/z＝640.15(C42H29BrN2＝641.60) Sub 1-3(22) m/z＝690.17(C46H31BrN2＝691.66)
Sub 1-3(23) m/z＝740.18(C50H33BrN2＝741.71) Sub 1-3(24) m/z＝944.28(C66H45BrN2＝945.98)
Sub 1-3(25) m/z＝639.13(C41H26BrN3＝640.57) Sub 1-3(26) m/z＝638.14(C42H27BrN2＝639.58)
Sub 1-3(27) m/z＝640.13(C40H25BrN4＝641.56) Sub 1-3(28) m/z＝744.12(C48H29BrN2S＝745.73)
Sub 1-3(29) m/z＝790.20(C54H35BrN2＝791.77) Sub 1-3(30) m/z＝790.20(C54H35BrN2＝791.77)
Sub 1-3(31) m/z＝714.17(C48H31BrN2＝715.68) Sub 1-3(32) m/z＝792.19(C52H33BrN4＝793.75)
Sub 1-3(33) m/z＝638.14(C42H27BrN2＝639.58) Sub 1-3(34) m/z＝638.14(C42H27BrN2＝639.58)
Sub 1-3(35) m/z＝714.17(C48H31BrN2＝715.68) Sub 1-3(36) m/z＝714.17(C48H31BrN2＝715.68)
Sub 1-3(37) m/z＝792.19(C52H33BrN4＝793.75) Sub 1-3(38) m/z＝870.17(C58H35BrN2S＝871.88)
Sub 1-3(39) m/z＝764.18(C52H33BrN2＝765.74) Sub 1-3(40) m/z＝714.17(C48H31BrN2＝715.68)
Synthesis example of Sub 1-5
Figure BDA0001266354490000261
The mixture of Sub1-3 (1) (7.9g, 16mmol), Sub 1-4(1) (5.5g, 18mmol), Pd (PPh)3)4(0.06g、0.05mmol)、K2CO3(6.6g, 48mmol) was dissolved in anhydrous THF and a small amount of water, and the above-mentioned synthesis method of Sub1-2(2) was used to obtain 3.9g (yield: 76%) of the product Sub 1-5 (1).
Example of Synthesis of Sub1
Figure BDA0001266354490000271
Sub 1-5(1) (6.4g, 12mmol) and triphenylphoshine were dissolved in o-dichlorobenzene and the reaction was allowed to circulate for 24 hours. After completion of the reaction, the solvent was removed by distillation under the reduced pressure, and the concentrated product was separated by column chromatography to obtain 4.7g (yield: 78%) of the desired product Sub1 (1).
On the other hand, although Sub1 is exemplified below, it is not limited thereto, and FD-MS thereof is shown in table 2 below.
Figure BDA0001266354490000272
Figure BDA0001266354490000281
[ TABLE 2 ]
Compound (I) FD-MS Compound (I) FD-MS
Sub 1(1) m/z＝501.22(C36H27N3＝501.62) Sub 1(2) m/z＝653.28(C48H35N3＝653.81)
Sub 1(3) m/z＝503.21(C34H25N5＝503.60) Sub 1(4) m/z＝577.25(C42H31N3＝577.72)
Sub 1(5) m/z＝653.28(C48H35N3＝653.81) Sub 1(6) m/z＝753.31(C56H39N3＝753.93)
Sub 1(7) m/z＝753.31(C56H39N3＝753.93) Sub 1(8) m/z＝957.41(C72H51N3＝958.20)
Sub 1(9) m/z＝575.24(C42H29N3＝575.70) Sub 1(10) m/z＝651.27(C48H33N3＝651.80)
Sub 1(11) m/z＝576.23(C41H28N4＝576.69) Sub 1(12) m/z＝681.22(C48H31N3S＝681.84)
Sub 1(13) m/z＝651.27(C48H33N3＝651.80) Sub 1(14) m/z＝751.30(C56H37N3＝751.91)
Sub 1(15) m/z＝751.30(C56H37N3＝751.91) Sub 1(16) m/z＝955.39(C72H49N3＝956.18)
Sub 1(17) m/z＝549.22(C40H27N3＝549.66) Sub 1(18) m/z＝651.27(C48H33N3＝651.80)
Sub 1(19) m/z＝500.20(C35H24N4＝500.59) Sub 1(20) m/z＝575.24(C42H29N3＝575.70)
Sub 1(21) m/z＝651.27(C48H33N3＝651.80) Sub 1(22) m/z＝701.28(C52H35N3＝701.85)
Sub 1(23) m/z＝751.30(C56H37N3＝751.91) Sub 1(24) m/z＝955.39(C72H49N3＝956.18)
Sub 1(25) m/z＝650.25(C47H30N4＝650.77) Sub 1(26) m/z＝649.25(C48H31N3＝649.78)
Sub 1(27) m/z＝651.24(C46H29N5＝651.76) Sub 1(28) m/z＝755.24(C54H33NS＝755.92)
Sub 1(29) m/z＝801.31(C50H39N3＝801.967) Sub 1(30) m/z＝801.31(C60H39N3＝801.97)
Sub 1(31) m/z＝825.28(C54H35N3＝725.88) Sub 1(32) m/z＝803.30(C58H37N5＝803.95)
Sub 1(33) m/z＝649.25(C48H31N3＝649.78) Sub 1(34) m/z＝649.25(C48H31N1＝649.78)
Sub 1(35) m/z＝725.28(C54H35N3＝725.88) Sub 1(36) m/z＝725.28(C54H35N3＝725.88)
Sub 1(37) m/z＝803.30(C58H37N5＝803.95) Sub 1(38) m/z＝881.29(C64H39N3S＝882.08)
Sub 1(39) m/z＝775.30(C58H37N3＝775.93) Sub 1(40) m/z＝725.28(C54H35N3＝725.88)
Sub 1(41) m/z＝691.30(C51H37N3＝691.86) Sub 1(42) m/z＝699.27(C52H33N3＝699.84)
Sub 1(43) m/z＝574.22(C41H26N4＝574.67) Sub 1(44) m/z＝575.24(C42H29N3＝575.70)
Sub 1(45) m/z＝573.22(C42H27N3＝573.68)
Sub 2 e.g.
The Sub 2 of the above reaction formula 1 is exemplified below, but not limited thereto.
Figure BDA0001266354490000301
Example of Synthesis of final Products (Products)
1.1 Synthesis example of 1-1
Figure BDA0001266354490000302
Put Sub1 (10.0g, 20mmol), Sub 2-1(3.5g, 22mmol), Pd2(dba)3(0.5g、0.6mmol)、P(t-Bu)3(0.2g, 2mmol), t-BuONa (5.8g, 60mmol), toluene (300mL), followed by reaction at a temperature of 100 ℃. When the reaction is complete, CH is used2Cl2Extracting with water, and then, extracting with MgSO4The organic layer was dried and concentrated, and silicagel column and recrystallization were carried out on the resulting compound to obtain 6.5g (yield: 65%) of the product (1-1).
2.2-5 Synthesis examples
Figure BDA0001266354490000303
Put Sub 1(41) (13.8g, 20mmol), Sub 2-1(3.5g, 22mmol), Pd2(dba)3(0.5g、0.6mmol)、P(t-Bu)3(0.2g, 2mmol), t-BuONa (5.8g, 60mmol) and toluene (300mL) were synthesized by the above-mentioned 1-1 synthesis method to obtain 9.5g (yield: 62%) of the product (2-5).
Examples of Synthesis of 3.3 to 9
Figure BDA0001266354490000311
Put Sub1 (11.0g, 20mmol), Sub 2-16(5.8g, 22mmol), Pd2(dba)3(0.5g、0.6mmol)、P(t-Bu)3(0.2g, 2mmol), t-BuONa (5.8g, 60mmol) and toluene (300mL) were synthesized by the above-mentioned 1-1 synthesis method to obtain 8.8g (yield: 60%) of the product (3-9).
4.4 examples of Synthesis of 13
Figure BDA0001266354490000312
Put Sub 1(42) (14.0g, 20mmol), Sub 2-1(3.5g, 22mmol), Pd2(dba)3(0.5g、0.6mmol)、P(t-Bu)3(0.2g, 2mmol), t-BuONa (5.8g, 60mmol) and toluene (300mL) were synthesized by the above-mentioned 1-1 synthesis method to obtain 9.8g (yield: 63%) of the product (4-13).
Examples of Synthesis of 5.5 to 5
Figure BDA0001266354490000313
Put Sub 1(43) (14.0g, 20mmol), Sub 2(1) (3.5g, 22mmol), Pd2(dba)3(0.5g、0.6mmol)、P(t-Bu)3(0.2g, 2mmol), t-BuONa (5.8g, 60mmol) and toluene (300mL) were synthesized by the above-mentioned 1-1 synthesis method to obtain 8.5g (yield: 65%) of the product (5-5).
Examples of 6.6 to 9 Synthesis
Figure BDA0001266354490000321
Put Sub 1(44) (11.5g, 20mmol), Sub 2-10- (5.8g, 22mmol), Pd2(dba)3(0.5g、0.6mmol)、P(t-Bu)3(0.2g, 2mmol), t-BuONa (5.8g, 60mmol) and toluene (300mL) were synthesized by the above-mentioned 1-1 synthesis method to obtain 8.9g (yield: 59%) of the product (6-9).
7.7 Synthesis examples of 7 to 7
Figure BDA0001266354490000322
Put Sub1 (15.0g, 20mmol), Sub 2-1(3.5g, 22mmol), Pd2(dba)3(0.5g、0.6mmol)、P(t-Bu)3(0.2g, 2mmol), t-BuONa (5.8g, 60mmol) and toluene (300mL) were synthesized by the above-mentioned 1-1 synthesis method to obtain 10.8g (yield: 65%) of the product (7-7).
Synthesis examples of 8.8 to 4
Figure BDA0001266354490000323
Put Sub1 (11.5g, 20mmol), Sub 2-17(6.0g, 22mmol), Pd2(dba)3(0.5g、0.6mmol)、P(t-Bu)3(0.2g, 2mmol), t-BuONa (5.8g, 60mmol) and toluene (300mL) were synthesized by the above-mentioned 1-1 synthesis method to obtain 9.2g (yield: 60%) of the product (8-4).
FD-MS of the compound of the present invention prepared in the above-described synthesis example are shown in table 3.
[ TABLE 3 ]
Figure BDA0001266354490000331
Figure BDA0001266354490000341
Figure BDA0001266354490000351
Evaluation of organic electroluminescent element production
[ example 1]Green organic electroluminescent element (luminescence auxiliary layer)
An organic electroluminescent element was prepared by a conventional method using the compound of the present invention as a light-emitting auxiliary layer substance. First, 4' -Tris [2-naphthyl (phenyl) amino is deposited on an ITO layer (anode) formed on an organic substrate in vacuum with a thickness of 60nm]After a hole injection layer was formed using triphenylamine (hereinafter, abbreviated as '2-TNATA'), N '-Bis (1-naphthyl) -N, N' -Bis-phenyl- (1,1'-biphenyl) -4,4' -diamine (hereinafter, abbreviated as 'NPB') was vacuum-deposited on the hole injection layer to a thickness of 60nm to form a hole transport layer. Next, after forming a light-emitting auxiliary layer by vacuum deposition of the compound 1-1 of the present invention on the hole transport layer in a thickness of 20nm, a host (host) of 4,4' -N, N ' -dicarbazole-biphenol (hereinafter, abbreviated as ' CBP ') was formed on the light-emitting auxiliary layer, and tris (2-phenylpyridine) -iridium (hereinafter, abbreviated as ' ir (ppy))3') as dopant (dopant), a compound doped with 95:5 by weight was vacuum deposited at a thickness of 30nm to form a light-emitting layer. Subsequently, (1,1' -biphenyl-4-olato) bis (2-methyl-8-quinonolato) aluminum (hereinafter, abbreviated as ' BAlq ') was vacuum-deposited on the light-emitting layer to a thickness of 10nm to form a hole-blocking layer, and tris- (8-hydroquinonol) aluminum (hereinafter, abbreviated as ' Alq ') was vacuum-deposited on the hole-blocking layer to a thickness of 40nm3') to form an electron transport layer. Then, LiF as an alkali halide was deposited in a thickness of 0.2nm to form an electron injection layer, and then aluminum (Al) was deposited in a thickness of 150nm to form a cathode, thereby preparing an organic electroluminescent element.
[ example 2]To [ example 28 ]]Green organic electroluminescent element (luminescence auxiliary layer)
An organic electroluminescent element was produced in the same manner as in example 1 above, except that one of the compounds of one embodiment of the present invention described in table 4 below was used as a light-emitting auxiliary layer substance instead of compound 1-1 of the present invention.
Comparative example 1
An organic electroluminescent element was produced in the same manner as in example 1 above, except that the light-emission auxiliary layer was not formed.
Comparative example 2]To [ comparative example 9]
An organic electroluminescent element was produced in the same manner as in example 1 above, except that one of comparative compound 1 to comparative compound 8 was used as a light-emitting auxiliary layer substance instead of compound 1-1 of the present invention.
Figure BDA0001266354490000361
The organic electroluminescent elements prepared in examples 1 to 28 and comparative examples 1 to 9 of the present invention were applied with a forward bias dc voltage, and Electroluminescent (EL) characteristics were measured using PR-650 of photoresearch corporation, and the life of T95 was measured using life measuring equipment prepared by mcccience corporation at a standard luminance of 5000 cd/square meter, and the measurement results are shown in table 4 below.
[ TABLE 4 ]
Figure BDA0001266354490000371
Figure BDA0001266354490000381
[ example 29]Red organic electroluminescent element (luminescence auxiliary layer)
The compound of the present invention is used for producing an organic electroluminescent element by a usual method using a substance of a hole transport layer. First, an ITO layer (anode) formed on an organic substrate was coated with a coating solution of 60 angstromsAfter 2-TNATA was deposited in a vacuum at a thickness of nm to form a hole injection layer, NPB was deposited in a vacuum at a thickness of 60nm on the hole injection layer to form a hole transport layer. Then, the compound 1-2 of the present invention was vacuum-evaporated on the hole transport layer to a thickness of 20nm to form a light-emitting auxiliary layer. Next, a bis- (1-phenylisoquinocyl) iridium (III) acetylacetate (hereinafter, abbreviated as' (piq)) was formed on the luminescence auxiliary layer mainly with CBP2Ir (acac)') as dopant, a mixture doped with 95:5 weight was vacuum deposited at a thickness of 30nm to form a light emitting layer. Then, a hole-blocking layer was formed by vacuum deposition of BALq on the light-emitting layer at a thickness of 10nm, and Alq was vacuum deposited on the hole-blocking layer at a thickness of 40nm3To form an electron transport layer. Then, LiF as an alkali halide was deposited in a thickness of 0.2nm to form an electron injection layer, and then aluminum (Al) was deposited in a thickness of 150nm to form a cathode, thereby preparing an organic electroluminescent element.
Example 30]To [ example 56]Red organic electroluminescent element (luminescence auxiliary layer)
An organic electroluminescent element was produced in the same manner as in example 29, except that one of the compounds according to one example of the present invention described in table 5 below was used as a light-emitting auxiliary layer substance in place of the compounds 1 to 2 according to the present invention.
Comparative example 10
An organic electroluminescent element was produced in the same manner as in example 29 above, except that the light-emission auxiliary layer was not formed.
Comparative example 11]To [ comparative example 18]
An organic electroluminescent element was produced in the same manner as in example 29 above, except that one of comparative compound 1 to comparative compound 8 was used instead of compound 1-2 of the present invention as a light-emitting auxiliary layer substance.
The organic electroluminescent elements prepared in examples 29 to 56 and comparative examples 10 to 18 of the present invention were applied with a forward bias dc voltage, and Electroluminescent (EL) characteristics were measured using PR-650 of photoresearch corporation, and the life of T95 was measured using life measuring equipment prepared by mcccience corporation at a standard luminance of 2500 cd/square meter, and the measurement results are shown in table 5 below.
[ TABLE 5 ]
Figure BDA0001266354490000401
Figure BDA0001266354490000411
As is clear from the results of the measurement of the elements in tables 4 and 5, it was confirmed that the light emission efficiency and the lifetime of the element using the compound according to one embodiment of the present invention as a material of the light emission auxiliary layer were significantly improved as compared with the elements using the comparative compounds 1 to 8 as a material of the light emission auxiliary layer and the elements without the light emission auxiliary layer.
It was confirmed that the light emission efficiency and the lifetime of the element having the light emission auxiliary layer formed thereon were significantly improved, although the driving voltage was slightly increased, compared to the element having no light emission auxiliary layer formed thereon (comparative example 1 and comparative example 10). Further, as the light emission auxiliary layer, the elements using comparative compound 8 in which N-carbazolyl groups are substituted at both the 1 st and 3 rd positions of the carbazolyl group (comparative examples 9 and 18) showed more excellent results than the elements using comparative compounds 1 to 7 (comparative examples 2 to 8 and 11 to 17), and it was confirmed that the elements using the compound according to an embodiment of the present invention substituted with arylamine or carbazolyl group showed the highest light emission efficiency and lifetime, except for the case where N-carbazolyl groups are substituted at both the 1 st and 3 rd positions of the carbazolyl group.
This is because, compared to the elements using comparative compounds 1 to 7 in which the amine group or carbazolyl group is substituted in the benzene ring on both sides of the carbazolyl group, compounds in which 2 substituents are substituted in the benzene ring on one side of the carbazolyl group, that is, the positions 1 and 3 of the carbazolyl group are substituted with the amine group or carbazolyl group have higher T1 and deeper HOMO levels, and thus electron blocking (electron blocking) ability and charge balance (charge balance) in the light emitting layer of holes and electrons are increased, and light emission is not well formed on the surface of the hole transport layer but inside the light emitting layer, and thus the efficiency and lifetime are maximized.
Further, it is suggested that, in view of the excellent device results of the compound of the present invention as compared with the comparative compound 8 in which the N-carbazolyl group is substituted at both the positions 1 and 3 of the carbazolyl group, the physical properties of the compound and the device results can be significantly different depending on the kind of the substituent in addition to the position of the substituent substituted by the carbazolyl group.
The above description is merely exemplary, and various modifications can be made by those skilled in the art without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed in the present specification are not intended to limit the present invention, but to illustrate the present invention, and the spirit and scope of the present invention are not limited by such embodiments. The scope of the invention should be construed in accordance with the appended claims, and all technical equivalents thereof should be construed as being included in the scope of the invention.
Cross reference to related patent applications
This patent application claims priority to korean patent application No. 10-2014-. If priority is claimed in this patent application for the same reason in other countries than the united states, the entire contents of the patent application are incorporated by reference.

Claims (12)

1. A compound represented by the following chemical formula 1:
chemical formula 1:
Figure FDA0003053501380000011
in the above-described chemical formula 1,
one of A and B is chemical formula 1-1 and the other is chemical formula 1-1 or chemical formula 1-2, wherein Ar is Ar in the case where A is chemical formula 1-11To Ar3Is benzene, L1Except for m-phenylene (meta-phenylene);
Figure FDA0003053501380000012
Ar1to Ar4Independently of one another, from the group: c6-C25And C comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P2-C16A heterocyclic group of (a);
L1and L2Independently of one another, from the group: single bond, C6-C18And C containing at least one hetero atom selected from the group consisting of O, N, S, Si and P2-C12A heterocyclic group of (a);
R1to R8Independently of each other
(i) Selected from the group consisting of: hydrogen, deuterium, halogen, C6-C60Aryl group, fluorenyl group, C containing at least one hetero atom selected from the group consisting of O, N, S, Si and P2-C60Heterocyclic group of (A), C1-C50Alkyl of (C)2-C20Alkenyl of, C2-C20Alkynyl of (A), C1-C30Alkoxy group of (A), and C6-C30Aryloxy group of or
(ii) R which is capable of forming at least one ring together with the benzene ring to which these are bonded by bonding between adjacent groups, in which case R which does not form a ring1To R8(ii) as defined in (i) above,
the aryl group, the fluorenyl group, the heterocyclic group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group, the aryloxy group, the arylene group and the fluorenylene group may be respectively selected from one of the following groupsSubstituted with the above substituents: heavy hydrogen, halogen, silyl, siloxane, boron, germanium, cyano, nitro, C1-C20Alkylthio of, C1-C20Alkoxy group of (C)1-C20Alkyl of (C)2-C20Alkenyl of, C2-C20Alkynyl of (A), C6-C20Aryl of (2), C substituted by deuterium6-C20Aryl group, fluorenyl group, C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P2-C20Heterocyclic group of (A), C3-C20Cycloalkyl of, C7-C20Arylalkyl of, and C8-C20The (a) aralkenyl group (b),
wherein the compound is not
Figure FDA0003053501380000021
2. The compound according to claim 1, wherein the chemical formula 1 is represented by one of the following chemical formula 2, chemical formula 3 and chemical formula 5,
Figure FDA0003053501380000022
in the above chemical formulas 2, 3 and 5, Ar1To Ar4、L1、L2And R1To R8The definitions in claim 1 are the same.
3. The compound according to claim 1, wherein the chemical formula 1 is one of the following compounds:
Figure FDA0003053501380000031
Figure FDA0003053501380000041
Figure FDA0003053501380000051
Figure FDA0003053501380000061
4. a compound represented by the following chemical formula 1:
chemical formula 1:
Figure FDA0003053501380000062
in the above-described chemical formula 1,
a and B are independently selected from the group consisting of: chemical formula 1-1, chemical formula 1-2, and chemical formula 1-3, except for the case where a and B are both chemical formula 1-3, and wherein i) one of a and B is chemical formula 1-3 and the other is chemical formula 1-1 or chemical formula 1-2, or ii) both a and B are chemical formula 1-2;
Figure FDA0003053501380000063
Ar1to Ar4Independently of one another, from the group: c6-C25And C comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P2-C16A heterocyclic group of (a);
L1to L3Independently of one another, from the group: single bond, C6-C18And C containing at least one hetero atom selected from the group consisting of O, N, S, Si and P2-C12A heterocyclic group of (a);
R1to R16Independently of each other
(i) Selected from the group consisting of: hydrogen, deuterium, halogen, C6-C60Aryl group, fluorenyl group, C containing at least one hetero atom selected from the group consisting of O, N, S, Si and P2-C60Heterocyclic group of (A), C1-C50Alkyl of (C)2-C20Alkenyl of, C2-C20Alkynyl of (A), C1-C30Alkoxy group of (A), and C6-C30Aryloxy group of or
(ii) R which is capable of forming at least one ring together with the benzene ring to which these are bonded by bonding between adjacent groups, in which case R which does not form a ring1To R16(ii) as defined in (i) above,
the above aryl group, fluorenyl group, heterocyclic group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, and fluorenylene group may be each substituted with one or more substituents selected from the group consisting of: heavy hydrogen, halogen, silyl, siloxane, boron, germanium, cyano, nitro, C1-C20Alkylthio of, C1-C20Alkoxy group of (C)1-C20Alkyl of (C)2-C20Alkenyl of, C2-C20Alkynyl of (A), C6-C20Aryl of (2), C substituted by deuterium6-C20Aryl, fluorenyl, C3-C20Cycloalkyl of, C7-C20Arylalkyl of, and C8-C20An aralkenyl group of (a).
5. The compound according to claim 4, wherein the above chemical formula 1 is represented by one of the following chemical formula 4, chemical formula 6 to chemical formula 9,
Figure FDA0003053501380000071
in the above chemical formula 4, chemical formula 6 toIn chemical formula 9, Ar1To Ar4、L1To L3And R1To R16The definitions in claim 4 are the same.
6. The compound according to claim 4, wherein the chemical formula 1 is one of the following compounds:
Figure FDA0003053501380000081
Figure FDA0003053501380000091
Figure FDA0003053501380000101
Figure FDA0003053501380000111
7. an organic electric element comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, wherein the organic layer has the compound represented by chemical formula 1 according to any one of claims 1 to 6.
8. The organic electric element according to claim 7, wherein at least one of the hole injection layer, the hole transport layer, the light-emission auxiliary layer, and the light-emitting layer of the organic layer contains one compound or two or more compounds of the compounds.
9. The organic electric element according to claim 7, further comprising a light efficiency improving layer formed on at least one of the first electrode and the second electrode, the one of the first electrode and the second electrode being opposite to the organic layer.
10. The organic electric element according to claim 7, wherein the organic layer is formed by a spin coating process, a nozzle printing process, an ink jet printing process, a slit coating process, a dip coating process, or a roll-to-roll process.
11. An electronic device, comprising:
a display device comprising the organic electric element of claim 7; and
and a control unit for driving the display device.
12. The electronic device according to claim 11, wherein the organic electric element is at least one of: organic electroluminescent elements, organic solar cells, organic photoreceptors, organic transistors, and elements for monochromatic or white illumination.
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